The long range objectives of the proposed research may be divided into two general categories. In the first phase, we plan to develop methods of synthesis and study mechanisms of reactions of 2-aroyl- and 2-arenesulfonyl allyl amines. Chemical data on these activated allylamino substrates will be utilized in the overall evaluation of these agents as potential anti-tumor agents. Additionally, bis-allylamino sulfonyl arenas and bis-allylamino aroyl substrates will be characterized. These polyfunctional alkylating agents are being examined as analogs of quinone methides, an important class of biologically active organic compounds. The 2-arenesulfonyl- and 2-aroylallylamino substrates represent a new class of alkylating agents that will be developed as general fluorescent probes for proteins and nucleic acids. We plan to examine in detail the reactivities of 2-(naphthalenesulfonly)2-(naphthoyl)- and 2-(phenanthroyl)-allylamino substrates toward oligopeptides, histones and nucleic acids. Derivatives of activated allylamino substrates containing two functional groups on the arene substituent will be synthesized. The second section of the research objectives deals with transformations of cyclophane dienes to carcinogen-like bridged annulenes and to rigid polyfunctional alkylating agents. We shall concentrate our efforts on the synthesis of (1, 5, 10) methano [41] annulene, its benzo derivative, and polyfunctional allylamino substances derived from it. Bis-sulfonate esters and bis-allylamino substrates derived from [9] metacyclophane diene will be synthesized and investigated in terms of their effect on physical properties of deoxyribonucleic acid (DNA). Another important objective of this component of the MBRS program is to introduce undergraduate and graduate students to basic and modern techniques of biochemical and chemical research.